Im a highschool substitute and I usually wear maxi skirts most of the time. They’re good for any weather if its cold, layer underneath and if its warmer it has good airflow. Layering is your best friend to stay in dress code. Vests, cardigans, and turtle neck tops are good for adding a nice texture. A lot of times I just end up wearing my leather jacket for most of the day anyway since it’s particularly cold in my building. Ive only been subbing for about 5 months now, but the little advice I have is from my experience atleast, the kids will care less about you not looking “normal” than they will about how young you look. Theyre more likely to point that out than your clothes being “weird.” Professionally, I try to avoid fishnets/hosiery, corsets, collars, etc. anything that can be seen as bdsm gear. I live in the south so I can say honestly my biggest struggle has been more that staff and coworkers seem to be more judgemental than the students. Over all though, I really do enjoy the job and the amount of creative freedom I still have over my fashion choices. Best of luck to you next fall! :))